Each year for the last seven years I have done at least one stupid, difficult thing on my bicycle (and a few things off of it) for no really good reason at all, except to do it. It started in August 2015 with a poorly planned ride 77 mile from Stamford to New Paltz for a burrito, followed by a 77 mile return ride that saw the return of the same burrito. Each ride since then has taught me something and one of those lessons was that doing long rides near the longest day of the year eliminates potential daylight issues – no need to even consider carrying lights. And hence, the “Longest Day, Longest Ride” was born.

These rides are now attempted alone, since they have outgrown my wife’s threshold for stupidity. Some past rides in Denver have required some support (mechanical fails and the lack of water in the plains east of Denver) but I was determined to be self-supported this year. My goal for this year’s ride was to break the 200 mile distance mark.

Lessons learned from past rides relate to nutrition, hydration, route planning (just because google maps thinks it’s a road, doesn’t mean it IS a road) and pacing. I picked a route that looped from Manhattan, through Harriman State Park up to New Paltz, then back on the East Side of the Hudson River using the Empire State Trail – precisely 200 miles. This was a relatively flat route with just 8,100 feet of climbing. As usual, I set up my spreadsheet to determine expected stopping locations and my overall time for the ride. I bring a printout with me so I can check that I am roughly on track throughout the ride.

The ride was planned for Saturday June 18th, but due to a delayed flight back to New York the night before, I didn’t get home until midnight. Starting an all-day bike ride on four hours sleep seemed even too ill-advised for LDLR, so I decided to take a day off work instead and shift it to the following Monday. That turned out to be an excellent move because the winds on that Saturday would surely have undermined my attempt.

Sunday night I checked off the items on my pre-ride checklist. I packed my nutrition, laid out my kit, double checked my tires, charged my eTap batteries and my Wahoo head unit. In bed by nine, my alarm was set for 4:15am. I woke on time, ate breakfast and set off on track at 5am. I expected to be home between 6pm and 7pm.

Early morning rides are a treat, though a little less so on a weekday. Orchards was closed at that time of morning, but I was right on track with my planned time. Harriman State Park was especially quiet and the descent down Arden Valley Road out of the park was a highlight for the day. From there I would my way north, jumping on the Heritage Trailway to Goshen where I stopped for a snack, still on track.

I use the various screens on my Wahoo to monitor my effort and track my progress. I find I am constantly tracking average speed, TSS, hourly averages as well as the map to make sure I don’t end up off the carefully planned route. From Goshen I headed north on Route 207. I wanted to use rail trails where I could. I had mapped myself towards the Wallkill Valley Rail Trail that would take me into New Paltz. There was no obvious cycling friendly way and I had chosen route 207, which turned out to be even worse than I had thought – no real shoulder at all and 55 mph traffic, including trucks.

If that wasn’t bad enough, it was at that moment, just 69 miles into my ride, that my Wahoo battery died without warning. This was a somewhat tricky section of turns on roads that I was unfamiliar with and traffic was stressing me out. I no longer had the route, I no longer had information on how hard I was pushing, when to eat and drink. My head unit had been set to stay backlit for 30 seconds after each time I pressed a button to change a screen. I set this up in spring when doing intervals in Central Park in the dark and forgot to change it back. So my incessant toggling of the screens for information meant that the screen had been backlit for a lot of the last 4 hours. Totally my fault and a lesson learned – yet again.

I stopped, checked my phone for directions, regrouped myself and got on with it. While I had to stop to check for directions frequently for the next hour or so, once I was on the Wallkill Valley Rail Trail, I knew exactly where I was and all turns necessary to get home on the route.

It cost me a little time, but I arrived in New Paltz, stopped for food (NOT a burrito) and a water refill, about 30-45 minutes behind schedule. From there it was all Empire State Trail. It’s awesome that we can ride so far on such great biking infrastructure that keeps us safe. A 15 mile section from Stormville to south of West Pawling was a constant 1% grade uphill. That doesn’t sound like much, and I didn’t know how fast or slow I was going or even whether I was actually going uphill. But I felt terrible. That was mile 120-135 and I was wondering whether I would make it. But the following gentle downhills were equally pleasing.

I took a brief rest, sitting in the shade on a park bench in Brewster before commencing down the North County trail. I knew at that point I was fifty miles from home, and it was familiar territory. I arrived home right on 7pm. A fourteen-hour day, of which probably thirteen was riding. It’s not on Strava, but it happened and now I can start to think about next year’s ride.